UN UNUSUAL PRODUCT OF THE REACTION OF l-PHENYL-3-(3,4-DIMETHOXYPHENYL)-3-(2-OXOCYCLOHEXYL)-1-PROPANONE WITH HYDROGEN SULFIDE AND ACIDS: 2α-PHENYL-2,4-ortho-(14,15-DIMETHOXYBENZO)-cis-1-THIADECALIN

Article abstract of DOI:10.1007/BF00519935

The reaction of 1-phenyl-3-(3,4-dimethoxyphenyl)-3-(2-oxocyclohexyl)-1-propanone with hydrogen sulfide and acids gives an intramolecular rearrangement product, 2α-phenyl-2,4-ortho-(14,15-dimethoxybenzo)-cis-1-thiadecalin in addition to the unusual products of disproportionation of intermediate 2-phenyl-4-(3,4-dimethoxyphenyl)-5,6-tetramethylene-4H-thiopyran, namely, 5,6-tetramethylenethiopyrilium salts and 2α-phenyl-4α-(3,4-dimethoxyphenyl)-cis-1-thiadecalin.The configurational and conformational assignments for the sulfides, their sulfoxides, and sulfones were made by 13C NMR spectroscopy.